It’s a gradual and gorgeous climb from downtown Boulder heading west up the Boulder Creek Path and Fourmile Canyon to the legendary Poor Man Road. Just a few miles of asphalt and gravel—and, in the winter months, ice and snow kissing not only your tires but also the cliffs and peaks all around—and the Poor Man challenge is yours for the taking. Even Poor Man is brief, really; just over a mile of malleable dirt, rising and turning while gleeful, masochistic cyclists, who make their way up Fourmile Canyon on all kinds of bikes, grind out the climb to earn the immaculately beautiful flight down Sunshine Canyon back to Boulder’s quaint city center.

Even the slowest riders, like myself, need under 15 minutes to knock out Poor Man’s twisty, rugged ascent, which makes subsequent climbs on paved roads seem much easier. But for newbies, especially those with lungs not used to Boulder’s mile-plus elevation, Poor Man is a humbling adventure. I was once one of those humbled newbies.

Having moved from San Francisco to Boulder what seems like ages ago, I was an avid, long time commuter with delusions of mountain-cycling grandeur, thinking that mastery—on a single-speed Kona Lanai built by Box Dog Bikes in the Mission of San Francisco’s steep, but short, hills would translate into slaying Colorado climbs with ease. But in a land where even hour-long lunchtime quickies include 2,000 feet of climbing, years of blasting up Duboce Avenue and other heart-bursting SF favorites meant nothing the first time I greeted Poor Man. Even on a 27-speed Marin hybrid.

At the first switchback, which offers a breathtaking view of the climb riders must complete before reaching Poor Man, I stepped off my Marin and walked for a minute. Maybe 40 yards later I walked a little again. This was repeated a few times more. Then, after trying in vain to get my wheels going up Poor Man’s unforgiving dirt incline once more, I started walked up the final, toughest gradient before I even knew the finish—a mile-long , flat, dirt-covered link to Sunshine Canyon—was in sight.

I hung my head. As I walked, my boss—a seasoned long-distance cyclist who has been in Boulder for over 30 years, save a few years in law school—rolled down Poor Man on his Pugsley fatbike, having already finished the climb, to check on me.

“Don’t show off,” I said with a wry grin, as he wheeled around and finished Poor Man’s final hill a second time.

The next day, and the day after that, I used my lunch break to cycle up to Poor Man alone and complete it without walking. At both turns I stood and breathed deep for one minute, resting but never walking. The following week I did the whole climb, including the way up the canyons from downtown Boulder, without stopping at all, using my lowest gears to finish Poor Man.

It’s incredible what a body can learn. Cycling, especially in Boulder—where choosing a ride on any given day feels like being a foodie who can order for free from any restaurant in New York—presents seemingly endless chances to surpass what you thought were your limits.

Within months of that first embarrassing Poor Man ride/walk, I no longer needed my granny gear to get up the final ascent. Lately, even when I take a mountain bike up Poor Man in winter, I complete the entire ride without even leaving my largest front chainring. My next goal is slaying Poor Man on a single-speed.

It’s been a proud, meaningful rite of passage, or a series of them. I’ve discovered a lot about myself alone on Poor Man Road, and in the canyons that lead to it. My legs pump; my lugs charge; in that hour away from my office, my mind intermittently focuses, wanders and grows.

December is the only month in which I haven’t climbed Poor Man, and sometimes I even think Poor Man is where I’d prefer to die, but perhaps a bench at the top with my name on it is a bit more rational.

After several years of regular Poor Man rides, I’ve met some fun paved challenges—like the Col de Jamen in Switzerland; Super Flagstaff in Boulder; and Mt. Tamalpais in Marin County, Calif.—that no doubt seemed more gentle because of my extensive experience on the Poor Man dirt. It’s become a familiar, helpful part of me, and I’ve become the cyclist who riders less familiar with extended climbs, as I once was, hate to love.

Editor’s note: This feature originally appeared in Issue #32 of Bicycle Times. To make sure you never miss a bike review, order a subscription and you’ll be ready for the everyday cycling adventure.

For instance, when my older brother, Jeff, visited Colorado for the first time, two years ago, he rented a 27-speed Trek mountain bike, having cycled off and on since our childhood in Pittsburgh and completed a couple of 150-mile two-day rides in Pennsylvania and Ohio.

On Jeff’s second day in Boulder, he happily followed me up Boulder Canyon and Fourmile Canyon on his rented Trek on the way to Poor Man Road.

“Make sure to save your lowest gears for Poor Man,” I turned around and said to him when we were about a mile from the sharp turn from Fourmile Canyon onto the dirt wall that kicks off Poor Man.

“Oh no,” I thought, and immediately recalled my first time up Poor Man, with my boss.

“Well, you can do it, Jeff,” I urged. “If you need to take a break at any point, just go ahead, no problem.”

A few moments of competitive brotherly silence, except for his heavy breathing, ensued. Before he was halfway up the first hill, Jeff got off his bike and started to walk. He didn’t get back on his bike until Poor Man’s mile-plus of dirt ascent had ended; I waited for him at the top. The first thing he said when he knew I was within earshot was, “I hate you.”

Then he smiled—not a wry smile but a real one—and said, “That was awesome. I’ll get in shape and ride the whole thing the next time I’m out here.”

Maybe I should’ve stopped, too, and walked with my brother. Maybe I should have given him more than one day to get used to the elevation. Maybe I wanted to show off. Mostly, I wanted to add to my Poor Man memories.

On the way up Fourmile, Dan and I happened upon an older cyclist, probably in his mid 50s, on a mountain bike; the white-haired, joyful man complemented Dan on his artisan late-’90s titanium road bike, and quipped that he could tell I was a Boulder cyclist when I saw that I take a big u-lock and panniers on a climb.

Last week I took a Denver friend, who had previously joined me on a Boulder-area ride up to Jamestown via Lee Hill and Lefthand Canyon, up Poor Man. He’d been “defeated” by Poor Man when he first moved to Boulder five years ago and sincerely felt haunted by the experience, which ended at the first turn, when he decided to roll back down the way he came and return to Boulder.

Two weeks ago, Dan told me it meant a lot to him to attempt Poor Man again after all those years, like it was a lingering injury he felt he could finally heal for.

On the way up Fourmile, Dan and I happened upon an older cyclist, probably in his mid 50s, on a mountain bike; the white-haired, joyful man complemented Dan on his artisan late-’90s titanium road bike, and quipped that he could tell I was a Boulder cyclist when I saw that I take a big u-lock and panniers on a climb. The man asked for directions to Poor Man Road, and I said, “Just ride with us.”

When we turned on to Poor Man and began the first dirt ascent, Dan and I joked that the end of the four-mile climb felt like taking someone up that first slow rise on a rollercoaster before it flings you into unknown terror. But the fear Dan felt, especially with his asthma struggles, was mostly fear of an unknown that wasn’t terrifying at all when he faced it again. And, as I told him when the Poor Man grind began, “It’s not that hard; it’ll be over before you know it.”

And it was. Dan completed the ride, from downtown Boulder up to Poor Man and the rocket burst down Sunshine Canyon without stopping once, save for the moment Poor Man’s dirt ascent was safely over. He smiled big, gave me a fist-bump, and hunched over as if to throw up.

After two or three minutes of laughing with Dan while he recovered, the older rider joined us in taking the dirt link to Sunshine Canyon. But just before Dan and I began the descent to downtown Boulder for coffee at Trident Café, our new friend made a snap decision to “blow off work” and go in the other direction, up Sunshine Canyon and over to Lefthand Canyon.

Of all the things I’ve learned on a bike ride, that moment provided perhaps the most obvious: I realized what I want to be when I grow up.